172325-01-8

Basic information

• Product Name: benzyl N-(diphenylmethylene)-L-threoninate
• Synonyms: benzyl N-(diphenylmethylene)-L-threoninate
• CAS NO: 172325-01-8
• Molecular Weight: 373.452
• Mol File: 172325-01-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: benzyl N-(diphenylmethylene)-L-threoninate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl N-(diphenylmethylene)-L-threoninate(172325-01-8)
• EPA Substance Registry System: benzyl N-(diphenylmethylene)-L-threoninate(172325-01-8)

Safety Data

• Hazardous Substances Data: 172325-01-8(Hazardous Substances Data)

Upstream product

• 1013-88-3 Benzophenone imine 
• 86088-59-7 L-threonine benzyl ester hemioxalate 
• 33640-67-4 (2S,3R)-threonine benzyl ester 
• 100-51-6 benzyl alcohol 

Relevant articles and documents

Glucuronidation of Serine and Threonine

The synthesis of N-diphenylmethylene-O-(methyl(2,3,4-tri-O-acetyl)-β-D-glucuronosyl)- threonine benzyl ester (2) and N-diphenylmethylene-O-(methyl(2,3,4-tri-O-acetyl)-α/β-D-glucuronosyl) -serine benzyl ester (3) by Hanessian's modification of the Koenigs-

Solid-phase synthesis of O-linked glycopeptide analogues of enkephalin

The synthesis of 18 N-α-FMOC-amino acid glycosides for solid-phase glycopeptide assembly is reported. The glycosides were synthesized either from the corresponding O'Donnell Schiff bases or from N-α-FMOC-amino protected serine or threonine and the appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. Reaction rates of D-glycosyl bromides (e.g., acetobromoglucose) with the L- and D-forms of serine and threonine are distinctly different and can be rationalized in terms of the steric interactions within the two types of diastereomeric transition states for the D/L and D/D reactant pairs. The N-α-FMOC-protected glycosides [monosaccharides Xyl, Glc, Gal, Man, GlcNAc, and GalNAc; disaccharides Gal-β(1-4)-Glc (lactose), Glc-β(1-4)-Glc (cellobiose), and Gal-α(1-6)-Glc (melibiose)] were incorporated into 22 enkephalin glycopeptide analogues. These peptide opiates bearing the pharmacophore H-Tyr-c[DCys-Gly-Phe-DCys]- were designed to probe the significance of the glycoside moiety and the carbohydrate-peptide linkage region in blood-brain barrier (BBB) transport, opiate receptor binding, and analgesia.